CHEBI:66749 - phomoxanthone A

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ChEBI Name phomoxanthone A
ChEBI ID CHEBI:66749
Definition A member of the class of xanthones that is a dimer isolated from Phomopsis. It exhibits cytotoxic, antimalarial and antitubercular activities.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C38H38O16
Net Charge 0
Average Mass 750.69870
Monoisotopic Mass 750.21599
InChI InChI=1S/C38H38O16/c1-15-11-25(45)29-31(47)27-23(43)9-7-21(33(27)53-37(29,13-49-17(3)39)35(15)51-19(5)41)22-8-10-24(44)28-32(48)30-26(46)12-16(2)36(52-20(6)42)38(30,54-34(22)28)14-50-18(4)40/h7-10,15-16,35-36,43-46H,11-14H2,1-6H3/t15-,16-,35-,36-,37+,38+/m1/s1
InChIKey OHHXJWHRQGZQJM-ACMZUNAXSA-N
SMILES C[C@@H]1CC(O)=C2C(=O)c3c(O)ccc(-c4ccc(O)c5C(=O)C6=C(O)C[C@@H](C)[C@@H](OC(C)=O)[C@@]6(COC(C)=O)Oc45)c3O[C@]2(COC(C)=O)[C@@H]1OC(C)=O
Metabolite of Species Details
Phomopsis (NCBI:txid34399) An endophytic fungus See: PubMed
Roles Classification
Biological Role(s): antitubercular agent
A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antitubercular agent
A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing phomoxanthone A (CHEBI:66749) has role antimalarial (CHEBI:38068)
phomoxanthone A (CHEBI:66749) has role antineoplastic agent (CHEBI:35610)
phomoxanthone A (CHEBI:66749) has role antitubercular agent (CHEBI:33231)
phomoxanthone A (CHEBI:66749) has role metabolite (CHEBI:25212)
phomoxanthone A (CHEBI:66749) is a acetate ester (CHEBI:47622)
phomoxanthone A (CHEBI:66749) is a biaryl (CHEBI:64459)
phomoxanthone A (CHEBI:66749) is a phenols (CHEBI:33853)
phomoxanthone A (CHEBI:66749) is a xanthones (CHEBI:51149)
IUPAC Name
(5R*,5'R*,6R*,6'R*,10aR*,10a'R*)-10a,10a'-bis[(acetyloxy)methyl]-1,1',8,8'-tetrahydroxy-6,6'-dimethyl-9,9'-dioxo-5,5',7,7',9,9',10a,10a'-octahydro-6H,6'H-4,4'-bixanthene-5,5'-diyl diacetate
Synonym Source
rel-[(5R,5'R,6R,6'R,10aR,10a'R)-5,5'-diacetoxy-1,1',8,8'-tetrahydroxy-6,6'-dimethyl-9,9'-dioxo-5,5',6,6',7,7',9,9'-octahydro-10aH,10a'H-4,4'-bixanthene-10a,10a'-diyl]bis(methylene) diacetate ChEBI
Registry Number Type Source
8966562 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11520217 PubMed citation Europe PMC
20839612 PubMed citation Europe PMC
Last Modified
19 July 2013
General Comment
2013-07-19 Absolute stereochemistry of the compound has not been determined.